Oleophilic composition comprising a powdery or granular substance having a hydrophilic surface and an aluminum chelate compound

ABSTRACT

An oleophilic composition comprising a powdery or granular substance having a hydrophilic surface and a surface modifier comprising an aluminum chelate compound of the formula (I): ##STR1## wherein R 1  is selected from hydrogen and C1-6 alkyl, R 2  is selected from methyl and phenyl, R 3  is selected from R 4  --, R 5  O-- and R 6  NH--, A is selected from R 7  O--, R 8  COO--, R 9  SO 3  --, R 10  OSO 3  --, ##STR2## R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12  and R 13  are C1-22 alkyl or C3-22 alkenyl, aryl, aralkyl or alkylaryl, R 3  may be the same as or different from R 7 , R 8 , R 9 , R 10 , R 11 , R 12  and R 13 , with the proviso that at least one of R 3 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R 13  is a substituent having at least 8 carbon atoms or a polymerizable alkenyl group, and m=0.5 to 2.7, n=0.3 to 2.5 and m+n=0.8 to 3.

This is a continuation of application Ser. No. 424,452, filed Sept. 27,1982.

BACKGROUND OF THE INVENTION

(1) Field of the Invention

This invention relates to an oleophilic composition and to a surfacemodifier for a powdery or granular substance having a hydrophilicsurface, such as a filler or pigment for polymeric compound. Moreparticularly, it relates to an oleophilic composition comprising apowdery or granular substance having a hydrophlic surface and 0.1% to20% by weight, based on the weight of the powdery or granular substanceand at least one aluminum chelate compound, the powdery or granularsubstance being treated with the aluminum chelate compound to modifythis hydrophilic surface and improve the dispersibility of the powderyor granular substance in an organic medium.

(2) Description of the Prior Art

Ordinarily, a filler or pigment for a polymeric compound (hereinafterreferred to as "filler or the like" for brevity) has hydrophilicfunctional groups and adsorbed water on the surface thereof whereby thesurface of the filler or the like is kept hydrophilic. Accordingly, thefiller or the like is poor in the oleophilic characteristic and it doesnot show good dispersibility or miscibility to organic media such aspaint vehicles, printing ink vehicles and polymeric compounds.Therefore, if the filler or the like is used as it is, the gloss oropacitying power of a paint or printing ink is degraded or the strengthof a composite plastic material is reduced. As means for eliminatingthis defect, many proposals have been made which include, for example, amethod in which a surface active agent or metal soap is added togetherwith the filler or the like and a method in which the filler or the likeis treated with an organic silane type coupling agent. Furthermore, theyinclude a method in which aluminum triacylate or its derivatives areincorporated in an organic medium to improve the dispersibility of thefiller or the like in said organic medium (see U.S. Pat. No. 3,294,686),a method in which the filler or the like is treated with a titaniumcompound containing a partially hydrolyzed group (see U.S. Pat. No.4,098,758 which issued on U.S. patent application Ser. No. 694,576 whichis a continuation of co-pending U.S. patent application Ser. No. 556,879filed Mar. 10, 1975 which, in turn, was a continuation-in-part of U.S.Patent application Ser. No. 460,331 filed Apr. 12, 1974) and a method inwhich the filler or the like is treated with an aluminum alcoholate of alower or higher alcohol or a partially acylated product thereof (seeU.S. Pat. No. 3,905,936). These known methods are effective forimproving the dispersibility of the filler or the like to some extent,but their modifying effect is not satisfactory, the production of themodifiers is not easy, they readily solidify or a large amount of asolvent is necessary because the solubility is poor.

SUMMARY OF THE INVENTION

It is therefore a primary object of the present invention to provide asurface modifier for a powdery or granular substance having ahydrophilic surface, which exhibits an improved surface-modifying effectwithout any of the foregoing defects.

In accordance with the present invention, there is provided a surfacemodifier for a powdery or granular substance having a hydrophilicsurface, which comprises at least one aluminum chelate compoundrepresented by the following general formula (1): ##STR3## wherein R¹ isat least one member selected from a hydrogen atom and an alkyl grouphaving 1 to 6 carbon atoms, R² is at least one member selected frommethyl and phenyl groups, R³ is at least one member selected from R⁴ --,R⁵ O-- and R⁶ NH--, A is at least one member selected from R⁷ O--, R⁸COO--, R⁹ SO₃ --, R¹⁰ OSO₃ --, ##STR4## R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰,R¹¹, R¹² and R¹³ stand for an alkyl group having 1 to 22 carbon atoms oran alkenyl, aryl, aralkyl or alkylaryl group having 3 to 22 carbonatoms, R³ may be the same as or different from R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹²and R¹³, with the proviso that at least one of R³, R⁷, R⁸, R⁹, R¹⁰, R¹¹,R¹² and R¹³ is a substituent having at least 8 carbon atoms or apolymerizable alkenyl group, and m and n are mean values per moleculewhich satisfy the requirements of m=0.5 to 2.7, n=0.3 to 2.5 and m+n=0.8to 3.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

Some of the aluminum chelate compounds used in the present invention arenovel.

The aluminum chelate compounds used in the present invention will now bedescribed in detail.

In the general formula (I), the group R¹ O-- should be reactive with thehydrophilic surface of the filler or the like on which a hydrophilicfunctional group such as a hydroxyl group or adsorbed water is present.A high reactivity is desirable for this group. A group R¹ O-- in whichR¹ has a long chain is not preferred because the reactivity is low.Thus, R¹ is selected from a hydrogen atom and an alkyl group having 1 to6 carbon atoms. It is preferred that R¹ be a hydrogen atom or anisopropyl, sec-butyl or isobutyl group. Hydrocarbon substituents R⁴through R¹³ in A and R³ in the general formula (I) are as defined above,and preferred examples of these substituents are methyl, ethyl, butyl,capryl, lauryl, myristyl, palmityl, cetyl, stearyl, oleyl,dodecylphenyl, benzyl, nonylphenyl, isopropenyl and allyl groups. Thesegroups R⁴ through R¹³ impart an oleophilic characteristic to the surfaceof the filler or the like. Accordingly, at least one of the groups R⁴through R¹³ should contain a substituent having at least 8 carbon atomsor a polymerizable alkenyl group. These groups R⁴ through R¹³ may besubstituted by a functional group such as an amino group or a hydroxylgroup.

In the general formula (I), m, n and 3-(m+n), which are valuesindicating the ratios of the respective substituents to the aluminumatom, are determined while the balance between the intensity of thereaction of the aluminum compound of the present invention with thehydrophilic surface of the filler or the like and the oleophiliccharacteristic to be imparted is taken into account.

More specifically, in the aluminum compound of the present invention, mas the mean value per molecule is 0.5 to 2.7, preferably 1 to 2, and nas the mean value per molecule is 0.3 to 2.5, preferably 0.5 to 2, andm+2 is 0.8 to 3. If the mean value of m is smaller than 0.5, thereactivity of the aluminum compound with the hydrophilic surface becomespoor because the proportion of the group R¹ O is too small. If the meanvalue of m exceeds 2.7, the reactivity is undesirably too high.

The aluminum chelate compounds used in the present invention include,for example, the following compounds.

(1) Mono-(oleyl 3-oxobutanoato-O¹,O³)-bis-(2-propanolato)-aluminum,

(2) Bis-(oleyl 3-oxobutanoato-O¹,O³)-mono-(2-propanolato)-aluminum,

(3) Mono-(oleyl3-oxobutanoato-O¹,O³)-mono-acrylatomono-(2-propanolato)-aluminum

(4) Mono-(ethyl3-oxobutanoato-O¹,O³)-mono-(oleato)-mono-(2-propanolato)-aluminum,

(5) Mono-(oleyl 3-oxobutanoato-O¹,O³)-mono-(ethyl3-oxobutanoato-O¹,O³)-mono-(2-propanolato)-aluminum,

(6) Mono-(isostearyl3-oxobutanoato-O¹,O³)-mono-(rhodinato)-mono-(2-propanolato)-aluminum,

(7) Mono-(lauryl 3-oxobutanoato-O¹,O³)-mono-(N-lauroylβ-alanato)-mono-(2-propanolato)-aluminum,

(8) (Dioctylphosphato-O)-(9-octadecenyl-3-oxobutanoato-O¹,O³)-(2-propanolato)-aluminum,

(9) (Dibutyl phosphato-O)_(1/2) -(butyl phosphato-O,O)_(1/4)-(9-octadecenyl 3-oxobutanoato-O¹,O³)-(2-propanolato)-aluminum,

(10) (Dioctyl phosphato-O)_(1/4) -(octyl phosphato-O,O)_(1/4)-(9-octadecenyl-3-oxobutanoato-O¹,O³)-(2-propanolato)-aluminum,

(11) (Dioctyl phosphato-O)_(1/4) -(octyl phosphato-O,O)_(1/4)-hydroxy-(9-octadecenyl 3-oxobutanoato-O¹,O³)-aluminum,

(12) (Dioctyl phosphato-O)_(1/2) -(octyl phosphato-O,O)_(1/4) -(ethyl3-oxobutanoato-O¹,O³)-(2-propanolato)-aluminum,

(13) (Dioctyl phosphato-O)_(3/8) -(octyl phosphato-O,O)_(3/8)-(9-octadecenyl 3-oxobutanamido-O¹,O³)-(2-propanolato)_(1/2) -aluminum,

(14) (2,2-Dioctyl pyrophosphato-O)-(9-octadecenyl3-oxobutanoato-O¹,O³)-(2-propanolato)-aluminum,

(15) (4-Dodecylphenyl sulfonato-O)-(9-octadecenyl3-oxobutanoato-O¹,O³)-(2-propanolato)-aluminum,

(16) (4-Dodecylphenyl sulfonato-O)-hydroxy-(9-octadecenyl3-oxobutanoato-O¹,O³)-aluminum,

(17) (Dodecyl sulfato-O)-(9-octadecenyl3-oxobutanoato-O¹,O³)-(2-propanolato)-aluminum,

(18) (4-Dodecylphenyl sulfonato-O)-(9-octadecenyl3-oxo-3-phenylpropionato-O¹,O³)-(2-propanolato)-aluminum,

(19) (Methyl sulfonato-O)-(9-octadecenyl3-oxobutanoato-O¹,O³)-(2-propanolato)-aluminum,

(20) (4-Dodecylphenylsulfonato-O)-(2,4-pentanedionato-O,O¹)-(2-propanolato)-aluminum, and

(21) (4-Dodecylphenyl sulfonato-O)-(octyl3-oxobutanamido-O¹,O³)-(2-propanolato)-aluminum.

For better illustration, the substituents of the foregoing compounds (1)through (21) are shown below.

    __________________________________________________________________________    R.sub.1 R.sub.2                                                                              R.sub.3                                                                              A                    m n                                __________________________________________________________________________    (1)                                                                              i-C.sub.3 H.sub.7                                                                  CH.sub.3                                                                             OC.sub.18 H.sub.35                                                                   Not present          2 1                                (2)                                                                              i-C.sub.3 H.sub.7                                                                  CH.sub.3                                                                             OC.sub.18 H.sub.35                                                                   Not present          1 2                                (3)                                                                              i-C.sub.3 H.sub.7                                                                  CH.sub.3                                                                             OC.sub.18 H.sub.35                                                                   OCOCHCH.sub.2        1 1                                (4)                                                                              i-C.sub.3 H.sub.7                                                                  CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                     OCOC.sub.17 H.sub.33 1 1                                (5)                                                                              i-C.sub.3 H.sub.7                                                                  CH.sub.3                                                                             OC.sub.18 H.sub.35                                                                   OCOCH.sub.2 COCH.sub.3                                                                             1 1                                (6)                                                                              i-C.sub.3 H.sub.7                                                                  CH.sub.3                                                                             OC.sub.18 H.sub.37                                                                    ##STR5##            1 1                                (7)                                                                              i-C.sub.3 H.sub.7                                                                  CH.sub.3                                                                             OC.sub.12 H.sub.25                                                                    ##STR6##            1 1                                (8)                                                                              i-C.sub.3 H.sub.7                                                                  CH.sub.3                                                                             OC.sub.18 H.sub.35                                                                    ##STR7##            1 1                                (9)                                                                              i-C.sub.3 H.sub.7                                                                  CH.sub.3                                                                             OC.sub.18 H.sub.35                                                                    ##STR8##            1 1                                (10)                                                                             i-C.sub.3 H.sub.7                                                                  CH.sub.3                                                                             OC.sub.18 H.sub.35                                                                    ##STR9##            1 1                                (11)                                                                             H    CH.sub.3                                                                             OC.sub.18 H.sub.35                                                                   "                    1 1                                (12)                                                                             i-C.sub.3 H.sub.7                                                                  CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                     "                    1 1                                (13)                                                                             i-C.sub.3 H.sub.7                                                                  CH.sub.3                                                                             NHC.sub.18 H.sub.35                                                                  "                    0.5                                                                             1                                (14)                                                                             i-C.sub.3 H.sub.7                                                                  CH.sub.3                                                                             OC.sub.18 H.sub.35                                                                    ##STR10##           1 1                                (15)                                                                             i-C.sub.3 H.sub.7                                                                  CH.sub.3                                                                             OC.sub.18 H.sub.35                                                                    ##STR11##           1 1                                (16)                                                                             H    CH.sub.3                                                                             OC.sub.18 H.sub.35                                                                    ##STR12##           1 1                                (17)                                                                             i-C.sub.3 H.sub.7                                                                  CH.sub.3                                                                             OC.sub.18 H.sub.35                                                                   OSO.sub.2OC.sub.12 H.sub.25                                                                        1 1                                (18)                                                                             i-C.sub.3 H.sub.7                                                                   ##STR13##                                                                           OC.sub.18 H.sub.35                                                                    ##STR14##           1 1                                (19)                                                                             i-C.sub.3 H.sub.7                                                                  CH.sub.3                                                                             OC.sub.18 H.sub.35                                                                   OSO.sub.2CH.sub.3    1 1                                (20)                                                                             i-C.sub.3 H.sub.7                                                                  CH.sub.3                                                                             CH.sub.3                                                                              ##STR15##           1 1                                (21)                                                                             i-C.sub.3 H.sub.7                                                                  CH.sub.3                                                                             NHC.sub.18 H.sub.35                                                                   ##STR16##           1 1                                __________________________________________________________________________

These aluminum compounds can be prepared, for example, according to thefollowing methods.

(1) An aluminum alkoxide such as aluminum isopropoxide or aluminumbutoxide is reacted with a β-keto ester. This reaction is expressed bythe following reaction formula: ##STR17##

(2) An aluminum alkoxide is reacted with a β-keto ester and an acidicphosphoric acid ester. This reaction is represented by the followingreaction formula: ##STR18##

(3) An aluminum alkoxide is reacted with sulfonic acid and a β-ketoester. This reaction is represented by the following reaction formula:##STR19##

The surface modifier of the present invention, which comprises theabove-mentioned aluminum compound, is used for modifying the hydrophilicsurface of the filler or the like. The amount of the aluminum compoundused for the modification is from 0.1 to 20% by weight, preferably 0.5to 3% by weight, based on the filler or the like. As the method fortreating the filler or the like with the aluminum compound of thepresent invention, there may be adopted a method in which the aluminumcompound is incorporated, as it is or after dilution with an appropriatediluent, with the filler or the like in a mixer, a method in which thealuminum compound and the filler or the like are incorporated in anorganic solvent and thereafter the solvent is removed therefrom, and amethod in which the aluminum compound is incorporated, as it is, in amixture of an organic solvent and the filler or the like.

As the filler or the like to be modified with the aluminum chelatecompound of the present invention, there can be mentioned inorganic andorganic fillers and pigments, such as calcium carbonate, kaolin, mica,aluminum hydroxide, titanium dioxide, silica, zinc yellow, red lead, rediron oxide, zinc flower, talc, carbon black, barium sulfate, magnesiumcarbonate, asbestos, glass fiber, Phthalocyanine Blue, QuinacridoneYellow and Lake Red C. Of course, substances that can be modified by thealuminum chelate compound of the present invention are not limited tothose exemplified above, and various substances having a hydrophilicsurface can be modified by the aluminum chelate compound of the presentinvention. As pointed out hereinbefore, by the substance having ahydrophilic surface is meant a substance having on the surface thereof ahydrophilic functional group such as a hydroxyl group or water ofcrystallization or adsorbed water.

The filler or the like having the surface modified by the aluminumcompound of the present invention can be applied to various organicmedia, which include, for example, vehicles for paints and printinginks, composed of drying oils such as linseed oil, tung oil and soybeanoil, synthetic drying oils such as dehydrated castor oil, maleic oil,styrenated oil and vinyl toluene-modified oil, natural and modifiedresins such as rosin, hardened rosin, polymerized rosin, rosin ester,maleic acid resin, shellac and casein, synthetic resins such as phenolicresin, xylene resin, modified alkyd resin, polyamide resin andcoumarone-indene resin, rubber derivative such as chlorinated rubber andcyclized rubber, or cellulose derivatives such as nitro cellulose andethyl cellulose; solvents and diluents such as hexane, toluene, xyleneand cellosolve; and molding polymeric compounds such as polyethyleneresin, polypropylene resin, polystyrene resin, polyvinyl chloride resin,polyester resin, polycarbonate resin, silicone resin, acrylic resin,fluorine resin, epoxy resin, ABS resin and BS resin.

The filler or the like having the surface modified with the aluminumchelate compound of the present invention can be applied, in combinationwith an organic medium as described above, to various articles such asprinting inks, paints, polyvinyl chloride plastic tiles, flame-retardantplastics containing a large amount of aluminum hydroxide or calciumcarbonate, and pollution-free plastics comprising a polyolefin resin andcalcium carbonate.

The filler or the like modified by the aluminum chelate compound of thepresent invention has various advantages. For example, when the modifiedfiller or the like is applied to a paint or printing ink, (1) thesharpness is improved, (2) the gloss or hiding power is increased and(3) the mixing time is shortened at the ink- or paint-manufacturingstep. When the modified filler or the like is used for plastics, (1) theamount of the filler or the like in corporated with the plastics isincreased, (2) the flowability is improved, (3) physical properties ofproducts are improved, and (4) the mixing time is shortened.

It is believed that these excellent effects are due to the fact thatsince the aluminum chelate compound of the present invention containsnot only a group reactive with a hydroxyl group or adsorbed water on thesurface of the filler or the like but also an oleophilic group bonded toa stable chelate, sulfonic acid or phosphoric acid ester group, thealuminum chelate compound has an improved compatibility with both theorganic medium and the filler or the like.

The present invention will now be described in detail with reference tothe following Examples that by no means limit the scope of theinvention. Incidentally, the compound numbers in the Examples correspondto the numbers of the compounds exemplified hereinbefore.

REFERENCE EXAMPLE 1 Preparation of Compound (1)

A four-neck flask equipped with a stirrer, a thermometer, a droppingfunnel and a cooler was charged with 204 g (1 mole) of aluminumisopropylate, and 370 g (1 mole) of oleyl acetoacetate was dropped fromthe dropping funnel with stirring over a period of 30 minutes while theliquid temperature was maintained at 50° to 60° C. After completion ofthe dropwise addition, the temperature was gradually elevated to 130°C., and at this temperature, reaction was carried out with stirringwhile distilling isopropanol formed by the reaction. After completion ofdistillation of isopropanol, the reaction was further conducted for 15minutes to obtain 415 g of the compound (1) in the form of an oilyliquid.

Aluminum Content: 5.44% (found), 5.45% (calculated)

REFERENCE EXAMPLE 2 Preparation of Compound (2)

A four-neck flask equipped with a stirrer, a thermometer, a droppingfunnel and a cooler was charged with 495 g (1 mole) of mono-(oleyl3-oxobutanoate-O¹,O³)-bis-(2-propanolate)-aluminum, and 351 g (1 mole)of oleyl acetoacetate was dropped from the dropping funnel at roomtemperature with stirring over a period of 30 minutes. After completionof the dropwise addition, the temperature was elevated to 130° C. byheating, and reaction was carried out with stirring while distillingisopropanol formed by the reaction. After completion of distillation ofisopropanol, the reaction was further conducted under reduced pressurefor 15 minutes to obtain 770 g of the compound (2) in the form of anoily liquid.

Aluminum Content: 3.49% (found), 3.43% (calculated)

REFERENCE EXAMPLE 3 Preparation of Compound (8)

A 2-liter four-neck flask equipped with a stirrer, a thermometer, adropping funnel and a cooler was charged with 204 g (1 mole) of aluminumisopropoxide and 400 ml of toluene, and 351 g (1 mole) of oleylacetoacetate was dropped from the dropping funnel at room temperaturewith stirring over a period of 30 minutes. Then, a solution of 322 g (1mole) of dioctyl phosphate in 300 ml of toluene was similarly addeddropwise. After completion of the dropwise addition, the mixture washeated and refluxed for 30 minutes. Toluene and isopropyl alcohol formedby reaction were distilled off under reduced pressure to obtain 757 g ofthe compound (8) in the form of an oily liquid.

Aluminum Content: 3.55% (found), 3.56% (calculated)

REFERENCE EXAMPLE 4 Preparation of Compound (15)

A 2-liter four-neck flask equipped with a stirrer, a thermometer, adropping funnel and a cooler was charged with 204 g (1 mole) of aluminumisopropoxide and 400 ml of toluene, and at room temperature withstirring, 352 g (1 mole) of oleyl acetoacetate and then 327 g (1 mole)of dodecyl benzenesulfonate were added dropwise from the droppingfunnel. After completion of the dropwise addition, the mixture washeated and refluxed for 30 minutes, and toluene and formed isopropylalcohol were distilled off under reduced pressure to obtain 762 g of thecompound (15) in the form of an oily liquid.

Aluminum Content: 3.64% (found), 3.54% (calculated)

Characteristic Infrared Absorptions: 1605 cm⁻¹ (C=0 of chelate), 1125cm⁻¹ and 1040 cm⁻¹ (SO₂)

REFERENCE EXAMPLE 5 Preparation of Compound (16)

In the same manner as described in Reference Example 4 oleylacetoacetate and dodecyl benzenesulfonate were added dropwise to thetoluene solution of aluminum isopropoxide. Then, a solution of 18 g (1mole) of water in 100 ml of isopropyl alcohol was added dropwise to themixture. After completion of the dropwise addition, the mixture washeated and refluxed for 30 minutes, and toluene and formed isopropylalcohol were distilled off under reduced pressure to obtain 721 g of thecompound (16) in the form of an oily liquid.

Aluminum Content: 3.85% (found), 3.75% (calculated)

Characteristic Infrared Absorptions: 3400 cm⁻¹ (OH), 1605 cm⁻¹ (C=0 ofchelate), 1125 cm⁻¹ and 1040 cm⁻¹ (SO₂)

REFERENCE EXAMPLE 6 Preparation of Compound (17)

In the same manner as described in Reference Example 4, reaction wascarried out by using 204 g (1 mole) of aluminum isopropoxide, 352 g (1mole) of oleyl acetoacetate and 266 g (1 mole) of dodecyl sulfate,whereby 702 g of the compound (17) was obtained in the form of an oilyliquid.

Aluminum Content: 3.77% (found), 3.85% (calculated)

Characteristic Infrared Absorptions: 1605 cm⁻¹ (C=0 of chelate), 1060cm⁻¹ (O--SO₂ --O)

EXAMPLE 1

The effect of improving the sharpness of a printing ink by the aluminumchelate compound of the present invention was examined.

Namely, the aluminum compound was added in an amount of 5% by weight toa commercially available ink, and the mixture was kneaded and thecolor-developing test was carried out.

From the naked eye comparison with the blank free of the aluminumcompound, it was found that the sharpness was apparently improved by thealuminum compound of the present invention.

This effect results in a definite difference of the reflectance on thesurface of a test piece for the color-developing test. Morespecifically, when the tristimulus values X, Y and Z were measured by acolor difference meter, it was found that the values corresponding tocomplementary colors of the respective inks were reduced. Namely, incase of the red ink, the value Z was reduced, in case of the blue ink,the vaue X was reduced, and in case of the black ink, the values X, Yand Z were reduced. Reduction ratios of the values X, Y and Z to thoseof the blank ink free of the aluminum compound are shown in Table 1.

                  TABLE 1                                                         ______________________________________                                                      Reduction Ratio                                                               (%)                                                             Aluminum Compound                                                                             X          Y     Z                                            ______________________________________                                         (1)            18         19    18                                            (8)             8         12     5                                            (9)             6         10    -3                                           (10)             4         10    -1                                           (11)             7          7     2                                           (16)            17         16    11                                           (17)            23         23    23                                           (19)            21         21    21                                           ______________________________________                                    

EXAMPLE 2

The effect of improving the dispersibility by the aluminum chelatecompound of the present invention was examined.

Namely, 0.03 g of the aluminum chelate compound of the presentinvention, 0.3 g of titanium dioxide and 30 ml of xylene were charged ina test tube, and the test tube was shaken to disperse titanium dioxidein xylene. The degree of sedimentation of titanium dioxide wasdetermined after the dispersion had been allowed to stand still for acertain time, and the relation between the standing time and the degreeof sedimentation was compared with the same relations observed in thecomparative and blank samples.

COMPARATIVE SAMPLES USED

Comparison (1): commercially available dispersant (diamine oleate)

Comparison (2): blank

Degree of sedimentation: (height of sedimented titanium dioxide/heightof solution)×100

The obtained results are shown in Table 2.

                  TABLE 2                                                         ______________________________________                                                   Standing Time (hours)                                              Aluminum Compound                                                                          0      6       24   48   72   120                                ______________________________________                                         (1)         100    98      91   80   67   50                                  (2)         100    98      90   80   60   40                                  (3)         100    98      90   78   57   31                                  (4)         100    98      90   80   67   40                                  (5)         100    98      92   83   73   56                                  (8)         100    98      90   70   60   30                                 (11)         100    98      88   65   46   25                                 (15)         100    98      85   72   58   37                                 (16)         100    98      86   74   64   43                                 (18)         100    98      85   73   62   41                                 (20)         100    98      84   69   57   36                                 (21)         100    98      85   73   63   43                                 Comparison (1)                                                                             100    100     50    2    2    2                                 Comparison (2)                                                                             100    100      2    2    2    2                                 ______________________________________                                    

EXAMPLE 3

The effect of reducing the viscosity of a dispersion of the filler orthe like by the aluminum compound of the present invention was examined.

More specifically, the compound (1) was mixed with calcium carbonate ata ratio shown in Table 3, and the mixture was sufficiently kneaded in amortar to effect the surface treatment of calcium carbonate. Theso-treated calcium carbonate was added to liquid paraffin and theviscosity was measured at 25° C. by a B-type rotational viscometer. Theobtained results are shown in Table 3.

                  TABLE 3                                                         ______________________________________                                        Ingredients                                                                   (parts by Composition No.                                                     weight)   1          2      3     4    5    6                                 ______________________________________                                        Calcium carbonate                                                                       50         50     67      67   67 67                                Liquid paraffin                                                                         50         50     33      33   33 33                                Compound (1)                                                                             0         0.5     0     0.5  1.0 2.0                               Viscosity (cP,                                                                          measurement                                                                              330    above 2,200                                                                              1,100                                                                              980                               25° C.)                                                                          impossible        100,000                                           ______________________________________                                    

EXAMPLE 4

The test was carried out in the same manner as described in Example 3 byusing the aluminum compound (1), dioctyl phthalate (DOP) and calciumcarbonate, and the viscosity was measured at 25° C. The obtained resultsare shown in Table 4.

                  TABLE 4                                                         ______________________________________                                        Ingredients                                                                   (parts by    Composition No.                                                  weight)      1          2      3        4                                     ______________________________________                                        Calcium carbonate                                                                          50         50     67         67                                  DOP          50         50     33         33                                  Compound (1)  0         0.5     0        1.0                                  Viscosity (cP, 25° C.)                                                              measurement                                                                              270    above 100,000                                                                          1,940                                              impossible                                                       ______________________________________                                    

EXAMPLE 5

The test was carried out in the same manner as described in Example 3 byusing the aluminum compound (1), liquid paraffin and titanium dioxide,and the viscosity was measured at 25° C. The obtained results are shownin Table 5.

                  TABLE 5                                                         ______________________________________                                        Ingredients  Composition No.                                                  (parts by weight)                                                                          1           2         3                                          ______________________________________                                        Titanium dioxide                                                                           50          50        50                                         Liquid paraffin                                                                            50          50        50                                         Compound (1)  0          1.0       2.0                                        Viscosity (cP, 25° C.)                                                              above 100,000                                                                             6,070     1,430                                      ______________________________________                                    

EXAMPLE 6

The test was carried out in the same manner as described in Example 3 byusing the aluminum compound (1), liquid paraffin and aluminum hydroxide,and the viscosity was measured at 25° C. The obtained results are shownin Table 6.

                  TABLE 6                                                         ______________________________________                                        Ingredients       Composition No.                                             (parts by weight) 1         2                                                 ______________________________________                                        Aluminum hydroxide                                                                              67        67                                                Liquid paraffin   33        33                                                Compound (1)       0        0.5                                               Viscosity (cP, 25° C.)                                                                   31,000    1,910                                             ______________________________________                                    

EXAMPLE 7

The viscosity-reducing effects by various aluminum compounds of thepresent invention were examined.

More specifically, 0.2 g of the aluminum compound of the presentinvention, 10 g of calcium carbonate and 10 g of liquid paraffin weresufficiently mixed in a mortar, and the viscosity was measured at 25° C.in the same manner as described in Example 3. The obtained results areshown in Table 7.

                  TABLE 7                                                         ______________________________________                                        Aluminum Compound No.                                                                          Viscosity (cP, 25° C.)                                ______________________________________                                         (2)             65                                                            (8)             68                                                            (9)             83                                                           (10)             85                                                           (12)             84                                                           (14)             63                                                           (15)             82                                                           (16)             68                                                           (17)             87                                                           (18)             70                                                           (19)             69                                                           Blank            measurement impossible                                                        because of too high                                                           viscosity                                                    ______________________________________                                    

EXAMPLE 8

In a Henschel mixer, 100 parts by weight of calcium carbonate having anaverage particle size of 2μ was treated with 3 parts by weight of thealuminum chelate compound of the present invention, and then, thetreated calcium carbonate was added to 100 parts by weight of a granularpolypropylene resin and the mixture was kneaded and pulverized for 10minutes by a two-roll mixer maintained at 177° C. The resultingpulverized composition was injection-molded into a plate at 200° C.under 5.1 kg/cm² for a mold-seal time of 30 seconds. The notched Izodimpact strength value of the molded plate was measured. The obtainedresults are shown in Table 8.

                  TABLE 8                                                         ______________________________________                                                         Notched Izod Impact                                          Aluminum Compound No.                                                                          Strength (kg · cm/cm)                               ______________________________________                                         (1)             4.5                                                          (10)             4.7                                                          (11)             4.2                                                          (15)             4.2                                                          (17)             4.0                                                          Blank            3.0                                                          ______________________________________                                    

I claim:
 1. An oleophilic composition comprising a powdery or granularsubstance having a hydrophilic surface and 0.1% to 20% by weight, basedon the weight of said powdery or granular substance, of at least onealuminum chelate compound represented by the following general formula(I): ##STR20## wherein R¹ is at least one member selected from ahydrogen atom and an alkyl group having 1 to 6 carbon atoms, R² is atleast one member selected from methyl and phenyl groups, R³ is at leastone member selected from R⁴ --, R⁵ O-- and R⁶ NH--, A is at least onemember selected from R⁷ O--, R⁸ COO--, R⁹ SO₃ --, R¹⁰ OSO₃ --, ##STR21##R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹² and R¹³ stand for an alkyl grouphaving 1 to 22 carbon atoms or an alkenyl, aryl, aralkyl or alkylarylgroup having 3 to 22 carbon atoms, R³ may be the same as or differentfrom R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹² and R¹³, with the proviso that at leastone of R³, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹² and R¹³ is a substituent having atleast 8 carbon atoms or a polymerizable alkenyl group, and m and n aremeans values per molecule which satisfy the requirements of m=0.5 to2.7, n=0.3 to 2.5 and m+n=0.8 to
 3. 2. The composition as set forth inclaim 1, wherein the aluminum chelate compound represented by thegeneral formula (I) is an aluminum chelate compound represented by thefollowing general formula (II) or (III): ##STR22## wherein R¹, R⁵, R⁷,R⁸, m and n are as defined in claim
 6. 3. The composition as set forthin claim 1, wherein the aluminum chelate compound represented by thegeneral formula (I) is an aluminum chelate compound having the followingchemical formula: ##STR23##
 4. The composition as set forth in claim 1,wherein the aluminum chelate compound represented by the general formula(I) is an aluminum chelate compound represented by the following generalformula (IV) or (V): ##STR24## wherein R¹, R², R³, R⁹, R¹⁰, m and n areas defined in claim
 6. 5. The composition as set forth in claim 1,wherein the aluminum chelate compound represented by the general formula(I) is an aluminum chelate compound represented by the following generalformula (VI), (VII) or (VIII): ##STR25## wherein R¹, R², R³, R¹¹, R¹²,R¹³, m and n are as defined in claim
 6. 6. The oleophilic composition asset forth in claim 1, wherein the powdery or granular substance is apigment.
 7. The oleophilic composition as set forth in claim 1, whereinsaid composition is a paint and the powdery or granular substance is apigment, and said composition further comprises a vehicle wherein thepigment and the aluminum chelate compound are dispersed.
 8. Thecomposition as set forth in claim 1, wherein the amount of the powderyor granular substance is between 0.5% to 3.0% by weight.
 9. Theoleophilic composition as set forth in claim 4, wherein the powdery orgranular substance is a pigment.
 10. The oleophilic composition as setforth in claim 5, wherein the powdery or granular substance is apigment.
 11. The oleophilic composition as set forth in claim 4, whereinsaid composition is a paint and the powdery or granular substance is apigment, and said composition further comprises a vehicle wherein thepigment and the aluminum chelate compound are dispersed.
 12. Theoleophilic composition as set forth in claim 5, wherein said compositionis a paint and the powdery or granular substance is a pigment, and saidcomposition further comprises a vehicle wherein the pigment and thealuminum chelate compound are dispersed.
 13. The composition as setforth in claim 4, wherein the amount of the powdery or granularsubstance is between 0.5% and 3.0% by weight.
 14. The composition as setforth in claim 5, wherein the amount of the powdery or granularsubstance is between 0.5% and 3.0% by weight.
 15. The composition as setforth in claim 9, wherein the amount of the powdery or granularsubstance is between 0.5% and 3.0% by weight.
 16. The composition as setforth in claim 10, wherein the amount of the powdery or granularsubstance is between 0.5% and 3.0% by weight.
 17. A paint compositioncomprising an oleophilic composition according to claim 1, comprising avehicle and wherein the powdery or granular substance is a pigment andis dispersed with the aluminum chelate compound.
 18. A paint compositioncomprising the composition of claim 1, and including a vehicle, andwherein the powdery or granular substance is a pigment.
 19. A paintcomposition comprising an oleophilic composition according to claim 4,comprising a vehicle and wherein the powdery or granular substance is apigment and is dispersed with the aluminum chelate compound.
 20. A paintcomposition comprising the composition of claim 5, and including avehicle, and wherein the powdery or granular substance is a pigment.